I will be heading down from Jacksonville later this week and will spend my 3 day weekend sailing in the beautiful Tampa Bay area (provided my job doesn't put a brake on my plans...)

I have recieved several excellent tips fom a few of the locals already, and now I am in the last phase of logistics planning. I just have to narrow down the best possible trips to maximize my precious time off of work. I will be busy on land for the first half of Saturday, but from Friday to Monday morning I am going to try to get in as much sailing as possible on my new (used) AI.

4. Spend Thursday night in Clearwater, then possibly do Caladesi/ Honeymoon Islands....don't have a route for that one, yet.

Can anyone give me a top 3 or top 5 personal favorite day sail to select from? My aim is a relatively easy day (I have sailed before, but only once on an AI on a day with no wind, otherwise, I'm a relative newbie).....I want to be able to pull up/sail to a few scenic sandbars/islands, and/or be able to stop at a cool watering hole (Tiki bar at Little Harbor brach I'm thinking, but I've never been on the water in Tampa, so I am only going by forum advice and google maps/images).

Is there anything I might be missing, or need to take into consideration (besides the daily monsoon, of course)?

Are there some area with the cheaper motels that I should really avoid? For that matter, does anyone have some hotel/motel recommendations?